Ethanol → HCID 21242087, compound

HRID 1761712Notes

Reaction equation

HRID 1761712 reaction equation
C([O:3][C:4]([C:6]1[CH:35]=[CH:34][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:21]4[CH:22]=[CH:23][C:24](=[O:27])[CH:25]=[CH:26][C:20]4=[C:19]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:18]=3)[CH2:13][CH2:12]2)=[CH:8][CH:7]=1)=[O:5])C.C(O)C.[OH-].[K+]>O>[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:21]4[CH:22]=[CH:23][C:24](=[O:27])[CH:25]=[CH:26][C:20]4=[C:19]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:18]=3)[CH2:13][CH2:12]2)=[CH:34][CH:35]=1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium Hydroxide2×HCID 21242091HCID 21242091, compound

Product 1

HCID 21242087HCID 21242087, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred suspension of 3-[4-(4-ethoxycarbonylbenzyl)-1-piperazinyl]-1-phenyl-7H-pyrrolo[1,2-a]azepin-7-one (1.2 g), prepared as described in Example 20, and ethyl alcohol (30 cc) under an atmosphere of nitrogen, a solution of potassium hydroxide (0.2 g) in distilled water (3 cc) is added at a temperature of about 20° C. in the course of 5 minutes. The reaction mixture is then heated to 60° C. for 4 hours. After the solution is cooled, 1N aqueous potassium hydroxide solution (10 cc) is added and the mixture is washed 3 times with methylene chloride (150 cc in total). The organic phases are combined, dried over anhydrous magnesium sulphate, filtered and evaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. The residue is dissolved in methylene chloride (5 cc) and the solution is poured into silica (40 g) contained in a column 1 cm in diameter. Elution is first performed with a mixture of cyclohexane and ethyl acetate (50:50 by volume) (2.5 liters) and the corresponding eluate is rejected. Elution is then performed with methanol (1 liter and the corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 1.7 kPa) at 40° C. After recrystallization in 2-methyl-2-butanol, 3-[4-(4-carboxybenzyl)-1-piperazinyl]-1-phenyl-7H-pyrrolo[1,2-a]azepin-7-one (0.6 g) is obtained in the form of its potassium salt.

Workup

  1. customprepared
  2. temperatureAfter the solution is cooled
  3. washthe mixture is washed 3 times with methylene chloride (150 cc in total)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C
  7. dissolutionThe residue is dissolved in methylene chloride (5 cc)
  8. additionthe solution is poured into silica (40 g)
  9. washElution
  10. additionis first performed with a mixture of cyclohexane and ethyl acetate (50:50 by volume) (2.5 liters)
  11. washElution
  12. customthe corresponding eluate is evaporated to dryness under reduced pressure (20 mm Hg; 1.7 kPa) at 40° C
  13. customAfter recrystallization in 2-methyl-2-butanol

Sources & evidence

ORD record
ord-f9ab933bd0a54b8a851fd26ea3e221b7
Source dataset
uspto-grants-1989_05
Patent number
US04826974

Reaction notes

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